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O-4310

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
O-4310
Clinical data
Other namesO4310; 1-Isopropyl-6-fluoropsilocin; 1-iPr-6-F-psilocin; 1-iPr-6-F-4-HO-DMT
Drug classSerotonin5-HT2A receptoragonist
Identifiers
  • 3-[2-(dimethylamino)ethyl]-6-fluoro-1-isopropyl-1H-indol-4-ol
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC15H21FN2O
Molar mass264.344 g·mol−1
3D model (JSmol)
  • CC(C)N1C2=CC(F)=CC(O)=C2C(CCN(C)C)=C1
  • InChI=1S/C15H21FN2O/c1-10(2)18-9-11(5-6-17(3)4)15-13(18)7-12(16)8-14(15)19/h7-10,19H,5-6H2,1-4H3
  • Key:PAUIFMSQKOHMQT-UHFFFAOYSA-N

O-4310, also known as1-isopropyl-6-fluoropsilocin (1-iPr-6-F-4-HO-DMT), is aserotonin receptoragonist of thetryptamine family.[1][2] It is the 1-isopropylated and 6-fluorinatedderivative of theserotonergic psychedelicpsilocin.[2]

Pharmacology

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The drug is said to be aserotonin5-HT2A receptor agonist and to be highlyselective for activation of this receptor over the closely related serotonin5-HT2B and5-HT2C receptors.[2] ItsEC50Tooltip half-maximal effective concentration at the serotonin 5-HT2A receptor was reported to be 5 nM and it was said to have anEmaxTooltip maximal efficacy of 89% relative to serotonin.[2] Conversely, O-4310 was said to be inactive at the serotonin 5-HT2B receptor, with noEC50 orEmax reported for this receptor, and was claimed to have anEC50 of 592 nM at the serotonin 5-HT2C receptor with anEmax of approximately 50%.[2] Hence, O-4310 appears to show about 118-fold selectivity for activation of the serotonin 5-HT2A receptor over the serotonin 5-HT2C receptor.[2]

Thepharmacodynamic activity of O-4310 was briefly described in apatent but not in the publishedscientific literature.[2][1] If the reported data are accurate, O-4310, along with other drugs like25CN-NBOH and(S,S)-DMBMPP, would be one of the most selective known agonists of the serotonin 5-HT2A receptor over the other serotonin5-HT2 receptors.[3]

History

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O-4310 was patented byBryan Roth and colleagues in 2006 and the patent was assigned to theAmericanpharmaceutical company Organix Inc.[2] The drug was also employed in ananimal study and described in the scientific literature by a group ofIranian researchers in 2017.[1]

See also

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References

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  1. ^abcMotaghinejad O, Motaghinejad M, Motevalian M, Rahimi-Sharbaf F, Beiranvand T (October 2017)."The effect of maternal forced exercise on offspring pain perception, motor activity and anxiety disorder: the role of 5-HT2 and D2 receptors and CREB gene expression".Journal of Exercise Rehabilitation.13 (5):514–525.doi:10.12965/jer.1734992.496.PMC 5667597.PMID 29114525.
  2. ^abcdefgh[url=https://patents.google.com/patent/US7655691B2/ US 7655691], Kumaran G, Morency C, Roth B, Sard HP, Shuster L Xu L, "Indole compounds useful as serotonin selective agents.", published 11 May 2006, assigned to Organix Inc and Tufts University, Case Western Reserve University 
  3. ^Poulie CB, Jensen AA, Halberstadt AL, Kristensen JL (December 2020)."DARK Classics in Chemical Neuroscience: NBOMes".ACS Chem Neurosci.11 (23):3860–3869.doi:10.1021/acschemneuro.9b00528.PMC 9191638.PMID 31657895.The psychedelic phenethylamines typically exhibit less than 5–10-fold selectivity for 5-HT2A over 5-HT2C receptors.53,54 Notable exceptions include (S,S)-DMBMPP and 25CN-NBOH (Figure 3), which are the most selective 5-HT2AR agonists published to date.49,58–61 (S,S)-DMBMPP exhibits more than 100-fold higher binding affinity for the 5-HT2AR over 5-HT2CR, and 25CN-NBOH has substantially higher agonist potencies at 5-HT2AR compared to 5-HT2CR.

External links

[edit]
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
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Tryptamines
4-Hydroxytryptamines
andesters/ethers
5-Hydroxy- and
5-methoxytryptamines
N-Acetyltryptamines
α-Alkyltryptamines
Cyclized tryptamines
Isotryptamines
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